EP0148119B1 - 2-Phenoxypropions ure-cyanamide - Google Patents

2-Phenoxypropions ure-cyanamide Download PDF

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Publication number
EP0148119B1
EP0148119B1 EP84810586A EP84810586A EP0148119B1 EP 0148119 B1 EP0148119 B1 EP 0148119B1 EP 84810586 A EP84810586 A EP 84810586A EP 84810586 A EP84810586 A EP 84810586A EP 0148119 B1 EP0148119 B1 EP 0148119B1
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EP
European Patent Office
Prior art keywords
formula
compounds
yloxy
propionic acid
phenoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP84810586A
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German (de)
English (en)
French (fr)
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EP0148119A2 (de
EP0148119A3 (en
Inventor
Beat Dr. Böhner
Hermann Dr. Rempfler
Rolf Dr. Schurter
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Novartis AG
Original Assignee
Ciba Geigy AG
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Publication date
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Priority to AT84810586T priority Critical patent/ATE42741T1/de
Publication of EP0148119A2 publication Critical patent/EP0148119A2/de
Publication of EP0148119A3 publication Critical patent/EP0148119A3/de
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Publication of EP0148119B1 publication Critical patent/EP0148119B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

  • the present invention relates to new herbicidally active 2-phenoxy-propionic acid cyanamides, processes for their preparation, further herbicidal compositions which contain these new compounds as active ingredients, and the use of the new active ingredients and the compositions containing them for the selective control of weeds in crop plants .
  • the invention also relates to new intermediates for the synthesis of the compounds according to the invention.
  • Herbicidal 2-phenoxypropionic acid amides with further substituents in the para position of the phenyl nucleus are known from the literature, such as, for example, German Offenlegungsschriften 2433067, 2531643, 2639796, 2640730 or 3004770 or the European patent application EP-A 21 453.
  • R and T used in the definition of the formula include, for example, the following substituents:
  • R generally represents hydrogen, methyl, ethyl, isopropyl, n-propyl, the four isomeric butyl, allyl, methallyl, 2- Butenyl, 3-butenyl, propargyl, 2-butynyl, 3-butynyl, methoxymethyl, methoxyethyl, ethoxymethyl and ethoxyethyl;
  • T generally represents a radical from the series phenyl, 2-pyridinyl, 2-quinolinyl, 2-quinoxalinyl, 2-benzoxazolyl or 2-benzothiazolyl which is at least substituted by the radical X.
  • R is preferably hydrogen or a saturated radical such as C 1 -C 4 alkyl or C 2 -C 4 alkoxyalkyl and T is a radical such as 2-benzoxazolyl or 2-quinoxaliny
  • the compounds in which R is C 1 -C 4 alkyl are preferred; in subgroup b) those in which either X for trifluoromethyl, Y for hydrogen and Z for the methine bridge; or X for trifluoromethyl, Y for hydrogen and Z for nitrogen; or X and Y for chlorine and Z for nitrogen; or X is chlorine, Y is fluorine and Z is nitrogen; ie T represents a radical from the group 4-trifluoromethylphenyl, 5-trifluoromethylpyridin-2-yl, 3,5-dichloropyridin-2-yl and 5-chloro-3-fluoropyridin-2-yl.
  • R is C 1 -C 4 -alkyl and T is either 4-trifluoromethylphenyl or 5-trifluoromethylpyridin-2-yl or 3,5-dichloropyridin-2-yl or 5-chloro-3-fluoropyridin-2-yl, the last type being preferred; or that R is C 1 -C 4 alkyl and T is 6-fluoro-quinoxalin-2-yl or 6-chloro-quinoxalin-2-yl; or that R is C 1 -C 4 alkyl and T is 6-chloro-benzoxazol-2-yl.
  • the compounds of the formula I according to the invention can be prepared by using a 2-phenoxypropionic acid halide of the formula II wherein T has the meaning given under formula I and Hal represents chlorine or bromine, in the presence of an acid-binding agent with a cyanamine of the formula III in which R has the meaning given under formula I.
  • the compounds of sub-formula la wherein T has the meaning given under formula I and R 1 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or C 2 -C 4 alkoxyalkyl can be obtained by a corresponding cyanamino compound of sub-formula Ib in which T has the meaning given under formula I, in the presence of an acid-binding agent, with a halogen compound of the formula IV Hal-R 1 (IV), in which R 1 has the meaning given under formula la and Hal represents chlorine, bromine or iodine .
  • the compounds of formula I according to the invention can also be obtained by using a phenoxypropionic acid derivative of formula V wherein R has the meaning given under formula I in the presence of an acid-binding agent with a halide of the formula VI T-Hal (VI) wherein T has the meaning given under formula and Hal represents fluorine, chlorine, bromine or iodine.
  • the compounds of formula I according to the invention are obtained by using a propionic acid derivative of formula VII wherein R has the meaning given under formula I and Hal represents chlorine, bromine, tosyl or mesyl, in the presence of an acid-binding agent with a hydroquinone derivative of the formula VIII in which T has the meaning given under formula I.
  • aprotic, inert organic solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as dimethyl amide amide or propionyl like dimethyl amide amide, or nitrile such as acetonitrile amide, or dimethyl amide, or nitrion such as acetonitrile amide, or nitrion such as acetonitrile amide, or nitrion such as acetonitrile amide, or dimethyl amide, or nitrion such as acetonitrile, such as acetonitrile amide, or dimethyl amide, or
  • Bases include, in particular, tertiary amines trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo- [4.3.0] non-5-ene or 1,8-diazabicyclo [5.4.0 ] -undec-7-en suitable.
  • inorganic bases such as hydrides such as sodium or calcium hydride, hydroxides such as sodium and potassium hydroxide, carbonates such as sodium and potassium carbonate or hydrogen carbonates such as potassium and sodium hydrogen carbonate can also be used as bases.
  • the propionic acid derivative of formula VII is obtained by using a propionic acid halide of the formula IX wherein Hal has the meaning given under formula VII and Hall stands for chlorine or bromine, in the presence of an acid-binding agent with a cyanamine of formula X in which R has the meaning given under formula VII.
  • the compounds of sub-formula VIIa can also be used first produce by the propionic acid halide of formula IX first in the presence of an acid-binding agent with cyanamine of formula XI and, if desired, reacting these compounds of the formula VIIa with an alkylating reagent which transfers the radical R 1 , as defined under formula IV.
  • the intermediates of formula V can be prepared from the compounds of formula VII by the compound of formula VII reacted with 4-benzyloxyphenol in the presence of a base and the product of formula XII obtained wherein R has the meaning given under formula I in the presence of a hydrogenation catalyst, such as palladium / carbon, treated with hydrogen.
  • a hydrogenation catalyst such as palladium / carbon
  • the new intermediates of the formulas V and VII are prepared by methods known per se.
  • the reaction conditions are chosen according to the requirements of the reagents used.
  • the intermediates of the formula XVIII can also be obtained by the compounds of the formula XIV in the presence of a base with a propionic acid ester of the formula XXI where Hal represents chlorine or bromine and alkyl represents C 1 -C 4 -alkyl.
  • reaction conditions for the reaction steps known per se such as catalysts, solvents and reaction temperatures, are known from the literature.
  • the compounds of formula 1 are obtained as racemates.
  • the invention relates to both enantiomers of the active compounds of the formula I and mixtures thereof. Unless a specific isomer is expressly mentioned, the statements made in the description always refer to the racemates.
  • the active ingredients of the formula are stable compounds. No precautionary measures are required to handle them.
  • the compounds of formula 1 are distinguished by good selective herbicidal properties, in particular against monocotyledon weeds, which make them excellent for use in crops of dicotyledonous crops, in particular cotton, soybean, rapeseed, sugar beet and fodder beet and sunflowers.
  • the compounds of formula 1 according to the invention can also be used as selective herbicides in monocotyledon crops such as cereals, for example wheat and barley. Weeds are sometimes damaged, which previously could only be dealt with with total herbicides.
  • the selective herbicidal activity of the compounds according to the invention is determined both in the preemergent and in the postemergent use. These active ingredients can therefore be used equally well in the pre-emergence and post-emergence procedures for selective weed control, in particular against harmful grasses.
  • the invention also relates to herbicidal compositions which contain a new active ingredient of the formula 1, and to processes for the pre- and post-emergence weed control of monocotyledonous plants, in particular grasses.
  • the compounds of the formula I are used in unchanged form or, preferably, as agents together with the auxiliaries customary in formulation technology and are therefore, for example, to emulsion concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules, also encapsulations in e.g. polymeric materials processed in a known manner.
  • the application methods such as spraying, atomizing, dusting, scattering or pouring, are selected in the same way as the type of agent, in accordance with the desired objectives and the given conditions.
  • the formulations i.e. the agents, preparations or compositions containing the active ingredient of formula I and optionally a solid or liquid additive are prepared in a known manner, e.g. by intimately mixing and / or grinding the active ingredients with extenders, e.g. with solvents, solid carriers, and optionally surface-active compounds (surfactants).
  • extenders e.g. with solvents, solid carriers, and optionally surface-active compounds (surfactants).
  • Possible solvents are: aromatic hydrocarbons, preferably the fractions C 8 to C 12 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters such as Ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.
  • aromatic hydrocarbons preferably the fractions C 8 to C 12 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate
  • solid carriers e.g. natural dust, such as calcite, talc, kaolin, montmorillonite or attapulgite
  • solid carriers e.g. natural dust, such as calcite, talc, kaolin, montmorillonite or attapulgite
  • highly disperse silica or highly disperse absorbent polymers can also be added.
  • adsorptive granulate carriers come porous types such as Pumice stone, broken brick, sepiolite or bentonite, as non-sorptive carrier materials e.g. Calcite or sand in question.
  • a large number of pregranulated materials of inorganic or organic nature such as, in particular, dolomite or comminuted plant residues can be used.
  • nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties are suitable as surface-active compounds.
  • surfactants are also to be understood as mixtures of surfactants.
  • Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.
  • the soaps are the alkali metal, alkaline earth metal or optionally substituted ammonium salts of higher fatty acids (C 10 -C 22 ), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures which, for example, from coconut or Tallow oil can be obtained.
  • the fatty acid methyl taurine salts should also be mentioned.
  • the fatty sulfonates or sulfates are usually present as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical with 8 to 22 carbon atoms, alkyl also including the alkyl part of acyl radicals, e.g. the Na or Ca salt of lignin sulfonic acid, dodecylsulfate or a fatty alcohol sulfate mixture made from natural fatty acids.
  • This subheading also includes the salts of sulfuric acid esters and sulfonic acids from fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2-sulfonic acid groups and a fatty acid residue with 8 to 22 carbon atoms.
  • Alkylarylsulfonates are e.g. the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a naphthalenesulfonic acid-formaldehyde condensation product.
  • Corresponding phosphates such as e.g. Salts of the phosphoric acid ester one
  • Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 10 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols .
  • nonionic surfactants are the water-soluble, 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups containing polyethylene oxide adducts with polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms in the alkyl chain, the compounds mentioned usually contain 1 to 5 units per propylene glycol unit glycol.
  • nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate, are also suitable.
  • the cationic surfactants are primarily quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and have low, optionally halogenated alkyl, benzyl or low hydroxyalkyl radicals as further substituents.
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. the stearyltrimethylammonium chloride or the benzyldi (2-chloroethyl) ethylammonium bromide.
  • the pesticidal preparations generally contain 0.1 to 95%, in particular 0.1 to 80% active ingredient of the formula I, 1 to 99.9% of a solid or liquid additive and 0 to 25%, in particular 0.1 to 25% of a surfactant.
  • the use forms can be diluted down to 0.001% of active ingredient.
  • the application rates are generally 0.01 to 10 kg ai / ha, preferably 0.025 to 5 kg ai / ha.
  • the agents can also contain other additives such as stabilizers, defoamers, viscosity regulators, binders, adhesives and fertilizers or other active ingredients to achieve special effects.
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water. The solutions are suitable for use in the form of tiny drops. The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated off in vacuo. Ready-to-use dusts are obtained by intimately mixing the carrier substances with the active ingredient.
  • results of the biological examples B1 and B2 are test results with the compound A, respectively which is known from DE-OS 3004770, page 12, No. 58, added.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP84810586A 1983-12-06 1984-11-30 2-Phenoxypropions ure-cyanamide Expired EP0148119B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT84810586T ATE42741T1 (de) 1983-12-06 1984-11-30 2-phenoxypropions ure-cyanamide.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH650983 1983-12-06
CH6509/83 1983-12-06
CH1948/84 1984-04-18
CH194884 1984-04-18

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP87117526A Division EP0305593A3 (de) 1983-12-06 1984-11-30 Neue Zwischenprodukte für 2-Pyridinyloxyphenoxypropionsäure-cyanamide
EP87117526.1 Division-Into 1987-11-27

Publications (3)

Publication Number Publication Date
EP0148119A2 EP0148119A2 (de) 1985-07-10
EP0148119A3 EP0148119A3 (en) 1986-07-02
EP0148119B1 true EP0148119B1 (de) 1989-05-03

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP84810586A Expired EP0148119B1 (de) 1983-12-06 1984-11-30 2-Phenoxypropions ure-cyanamide
EP87117526A Withdrawn EP0305593A3 (de) 1983-12-06 1984-11-30 Neue Zwischenprodukte für 2-Pyridinyloxyphenoxypropionsäure-cyanamide

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP87117526A Withdrawn EP0305593A3 (de) 1983-12-06 1984-11-30 Neue Zwischenprodukte für 2-Pyridinyloxyphenoxypropionsäure-cyanamide

Country Status (10)

Country Link
US (2) US4640703A (ro)
EP (2) EP0148119B1 (ro)
AU (2) AU578918B2 (ro)
BR (1) BR8406214A (ro)
CA (2) CA1244428A (ro)
DE (1) DE3478024D1 (ro)
ES (2) ES8609220A1 (ro)
HU (1) HU192627B (ro)
IL (1) IL73738A (ro)
RO (2) RO92723B (ro)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0148119B1 (de) 1983-12-06 1989-05-03 Ciba-Geigy Ag 2-Phenoxypropions ure-cyanamide
DE3536664A1 (de) * 1985-10-15 1987-04-16 Basf Ag Diphenyletherderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unerwuenschtem pflanzenwachstum
US4897481A (en) * 1988-05-31 1990-01-30 The Dow Chemical Company Process for the minimization of racemization in the preparation of optically active ((aryloxy)phenoxy)propionate herbicides
US4910309A (en) * 1988-07-08 1990-03-20 The Dow Chemical Company Enrichment of optical of 2-(4-aryloxyphenoxy)-propionic acids by crystallization as hydrates
US5316856A (en) * 1988-12-03 1994-05-31 Ngk Spark Plug Co., Ltd. Silicon nitride base sintered body
US5274100A (en) * 1990-10-23 1993-12-28 Ciba-Geigy Corporation Process for the preparation of (3-fluoropyridin-2-yloxy)phenoxypropionic acids
KR100212690B1 (ko) * 1990-10-23 1999-08-02 더블류. 하링, 지. 보이롤 (3-플루오로피리딘-2-일옥시)페녹시프로피온산의 제조방법
TW561153B (en) * 1998-07-25 2003-11-11 Dongbu Hannong Chemical Co Ltd Herbicidal phenoxypropionic acid N-alkyl-N-2-fluoro-phenyl amide compounds
KR20030065644A (ko) * 2002-01-30 2003-08-09 동부한농화학 주식회사 일년생 및 다년생 화본과 잡초 방제에 유효한 농약 조성물
CN107382896B (zh) * 2017-08-02 2019-07-09 张建华 苯并噁唑-2-氧基苯氧基丙酰亚胺类化合物及其合成方法与应用
CN112250621A (zh) * 2020-09-23 2021-01-22 甘肃联凯生物科技有限公司 炔草酯的合成方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2433067B2 (de) 1974-07-10 1977-11-24 a- [4-(4" Trifluormethylphenoxy)-phenoxy] -propionsäuren und deren Derivate, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel Hoechst AG, 6000 Frankfurt Alpha- eckige klammer auf 4-(4' trifluormethylphenoxy)-phenoxy eckige klammer zu -propionsaeuren und deren derivate, verfahren zu ihrer herstellung und diese enthaltende herbizide mittel
CS185694B2 (en) 1974-07-17 1978-10-31 Ishihara Sangyo Kaisha Herbicidal agent
GB1560416A (en) 1975-09-03 1980-02-06 Rohm & Haas Trifluoromethylphenyl derivatives
US4133675A (en) * 1976-07-23 1979-01-09 Ciba-Geigy Corporation Pyridyloxy-phenoxy-alkanecarboxylic acid derivatives which are effective as herbicides and as agents regulating plant growth
DE2640730C2 (de) * 1976-09-10 1983-08-25 Hoechst Ag, 6230 Frankfurt Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel
EP0001473B1 (en) 1977-08-12 1988-07-27 Imperial Chemical Industries Plc Herbicidal halogenomethyl--pyridyloxy-phenoxy-alkanecarboxylic acids and derivatives, and processes of controlling unwanted plants therewith
EP0003648A3 (en) * 1978-02-15 1979-09-05 Imperial Chemical Industries Plc 4-aryloxy-substituted phenoxypropionamide derivatives useful as herbicides, compositions containing them, and processes for making them
JPS6033389B2 (ja) * 1979-02-22 1985-08-02 日産化学工業株式会社 複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤
US4505743A (en) * 1981-12-31 1985-03-19 Ciba-Geigy Corporation α-[4-(3-Fluoro-5'-halopyridyl-2'-oxy)-phenoxy]-propionic acid derivatives having herbicidal activity
IL68822A (en) * 1982-06-18 1990-07-12 Dow Chemical Co Pyridyl(oxy/thio)phenoxy compounds,herbicidal compositions and methods of using them
US4550192A (en) * 1983-09-01 1985-10-29 The Dow Chemical Company Fluorophenoxyphenoxypropionates and derivatives thereof
ZA848416B (en) * 1983-11-10 1986-06-25 Dow Chemical Co Fluorophenoxy compounds,herbicidal compositions and methods
EP0148119B1 (de) 1983-12-06 1989-05-03 Ciba-Geigy Ag 2-Phenoxypropions ure-cyanamide

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CA1244428A (en) 1988-11-08
US4640703A (en) 1987-02-03
EP0148119A2 (de) 1985-07-10
CA1284660C (en) 1991-06-04
IL73738A (en) 1988-08-31
HU192627B (en) 1987-06-29
ES8609220A1 (es) 1986-08-01
EP0305593A3 (de) 1989-10-11
EP0305593A2 (de) 1989-03-08
ES549070A0 (es) 1986-10-16
IL73738A0 (en) 1985-03-31
AU578918B2 (en) 1988-11-10
EP0148119A3 (en) 1986-07-02
DE3478024D1 (de) 1989-06-08
HUT36663A (en) 1985-10-28
ES8700243A1 (es) 1986-10-16
US4759796A (en) 1988-07-26
ES538263A0 (es) 1986-08-01
AU3630584A (en) 1985-06-13
BR8406214A (pt) 1985-10-01
RO89785A (ro) 1986-07-30
RO92723B (ro) 1987-12-01
RO92723A (ro) 1987-11-30
AU1974388A (en) 1988-10-20

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